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PODCAST

Side Hustle School

Chris Guillebeau / Onward Project

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who"s started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books. Sales and Distribution by Lemonada Media

business entrepreneurship

All Episodes

6:00

Ep. 3250 - First $1,000: Digital Window Menu Boards...

Side Hustle School ·

2025/11/24

In this week’s First $1,000 segment, a designer helps food trucks and pop-up restaurants get rid of chalk dust and update to the digital age. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions

en

7:07

Ep. 3249 - Weekend Workshop: From Ski Bum to...

Side Hustle School ·

2025/11/23

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: an online snow-skiing school. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show

en

5:18

Ep. 3248 - Q&A: “Should I spend $2,000 on retention...

Side Hustle School ·

2025/11/22

Today’s caller runs a tiny subscription app and has two grand to spend. Should that money patch cancelations or chase new sign-ups? We’ll do the napkin math and land on a clear next step. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com

en

5:25

Ep. 3247 - Q&A: “Instagram, TikTok, or LinkedIn—how...

Side Hustle School ·

2025/11/21

Posting everywhere spreads you thin; posting in the right place compounds momentum. Today we break down a three-question filter that shows exactly where this side hustler’s wallets should live first. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

5:38

Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their...

Side Hustle School ·

2025/11/20

In this week’s Throwback Thursday segment, hear how one copy-savvy side hustler turned a collection of recruiter emails into a paid “swipe file,” and then built a monthly subscription around it. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

6:49

Ep. 3245 - STORY: Six-Figure Beekeeping Biz Buzzes...

Side Hustle School ·

2025/11/19

The buzzworthy journey of Minnesotan bees and their keepers. These hardy bees don’t mess around—last year they produced $150,000 in sweet profits. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

4:26

Ep. 3244 - Q&A: “How do I upsell without sounding...

Side Hustle School ·

2025/11/18

Great contracting work often reveals the next problem to solve. Here’s a simple script that turns an “upsell” into an obvious win for the client—and leaves everyone feeling good about the extra invoice. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

6:20

Ep. 3243 - First $1,000: Cozy Reading Gadget Turns...

Side Hustle School ·

2025/11/17

A bedtime-reading addict bend a paperclip into a page holder, refines it into a soft-touch clip, and flips his ledger from red ink to a four-figure win. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions

en

8:08

Ep. 3242 - Weekend Workshop: “Digital Documentation”...

Side Hustle School ·

2025/11/16

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: how a single PDF guide earned $120,000 in its first year. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A

en

6:05

Ep. 3241 - Q&A: “Is remote-worker visa consulting a...

Side Hustle School ·

2025/11/15

Remote-worker visas are booming—and bewildering. Today we price a “visa concierge,” unpack simple liability safeguards, and gauge whether the market can pay more than pocket change. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com

en

5:22

Ep. 3240 - Q&A: “Should I tell my clients I’m using AI?”

Side Hustle School ·

2025/11/14

AI tools can double your output, but not everyone’s comfortable with it. Today we map a three-part policy for disclosing AI use that keeps trust high, quality higher, and clients on board. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on

en

6:00

Ep. 3239 - TBT: This Tiny Spreadsheet Tool Pays the Rent

Side Hustle School ·

2025/11/13

In this week’s Throwback Thursday segment, meet a side hustler who built a simple browser-based spreadsheet tool. It earns enough to cover his rent each month! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

7:25

Ep. 3238 - STORY: Agricultural Teacher Earns $200,000...

Side Hustle School ·

2025/11/12

After creating course materials for a forgotten group of educators, this agricultural teacher now earns a significant income from a growing business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions

en

4:41

Ep. 3237 - Q&A: “Will professionals trade hours...

Side Hustle School ·

2025/11/11

Can busy side hustlers trade skills instead of dollars? Today we outline a lean time-bank model—simple rules, low overhead, and real incentives to keep everyone honest. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

5:58

Ep. 3236 - First $1,000: Turning Cable Chaos into...

Side Hustle School ·

2025/11/10

Tired of cables dangling each time your standing desk rises? A quick TikTok clip of magnetic rails snapping cords into place sparked a rush of orders for this savvy side hustler. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

8:15

Ep. 3235 - Weekend Workshop: The Wandering Teacher's...

Side Hustle School ·

2025/11/09

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: an early language hacker starts “Fluent in 3 Months.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener

en

5:35

Ep. 3234 - Q&A: “What’s a fair founder-investor deal...

Side Hustle School ·

2025/11/08

Cash can launch the product; labor will keep it alive. Today we map out founder-friendly splits, vesting schedules, and a simple “dynamic equity” formula that grows with effort. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the

en

4:56

Ep. 3233 - Q&A: “Where do I find my first paying...

Side Hustle School ·

2025/11/07

One sale beats a hundred compliments. Let’s walk through a low-risk, weekend-ready plan that puts money in this side hustler’s hands within two weeks. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

6:00

Ep. 3232 - TBT: The Garage Gym Hustle That Went Digital

Side Hustle School ·

2025/11/06

In this week’s Throwback Thursday segment, learn how one fitness fan turned flipping gym equipment into a small media business. He now sells setup guides and curates weekly home gym deals for thousands of subscribers. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

8:25

Ep. 3231 - STORY: The Coffee Grinder That Made $300,000

Side Hustle School ·

2025/11/05

Rise and shine! A petroleum engineer finds the perfect item to resell on Amazon. He goes on to sell $300,000 worth of the humble coffee grinder. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect

en

1,328 results

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